Toluene → bis(3,5-Dimethylcyclohexyl)phthalate

HRID 1701464노트

반응식

HRID 1701464 반응식
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH3:12][CH:13]1[CH2:18][CH:17]([CH3:19])[CH2:16][CH:15]([OH:20])[CH2:14]1.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24](S(O)(=O)=O)=[CH:23][CH:22]=1.[C:32]1(C)C=CC=CC=1>O>[CH3:12][CH:13]1[CH2:18][CH:17]([CH3:19])[CH2:16][CH:15]([O:20][C:4](=[O:5])[C:3]2[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:1]([O:6][CH:23]2[CH2:24][CH:25]([CH3:32])[CH2:26][CH:21]([CH3:31])[CH2:22]2)=[O:11])[CH2:14]1

참가 물질

6

반응물 4

HCID 1140Toluene2회HCID 6101p-Toluenesulfonic acidHCID 6811Phthalic AnhydrideHCID 215843,5-Dimethylcyclohexan-1-ol

생성물 1

HCID 20751009bis(3,5-Dimethylcyclohexyl)phthalate

시약·촉매·용매 1

HCID 962Water용매

실험 절차

100 ml of toluene was added to a mixture of 44.4 g (0.3 mol) of phthalic anhydride, 83.3 g (0.66 mol) of 3,5-dimethylcyclohexanol and 2 g of p-toluenesulfonic acid and the mixture was refluxed with heating for 12 hours with the azeotropic removal of 6 ml of water. After the reaction, the mixture was cooled and 200 ml of toluene was added to the mixture. The organic solvent layer was washed with water, a 5% aqueous solution of sodium hydroxide and water, in this order and dried with anhydrous sodium sulfate. After filtering the mixture, the filtrate was concentrated under reduced pressure. 50 ml of hexane was added to the concentrate and column chromatographed to obtain the desired compound. The carrier used was 800 g of Silica Gel 60 manufactured by Merck Co. Hexane and hexane-diethyl ether (9:1 in volume ratio) were used as the solvent and 105.7 g (yield 91.2%) of Compound (5) was obtained from the hexane-diethyl ether eluate.

후처리

  1. temperaturethe mixture was refluxed
  2. customAfter the reaction
  3. temperaturethe mixture was cooled
  4. washThe organic solvent layer was washed with water
  5. dry with materiala 5% aqueous solution of sodium hydroxide and water, in this order and dried with anhydrous sodium sulfate
  6. filtrationAfter filtering the mixture
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. addition50 ml of hexane was added to the
  9. concentrationconcentrate
  10. customcolumn chromatographed

출처 및 근거

ORD 기록
ord-30b75737d8764cd18a84186f1e117dd2
출처 데이터셋
uspto-grants-1980_03
특허 번호
US04193802

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